CZ84095A3 - Process of stereoselective preparation of beta-phenylisoserin derivative and its use for preparation of taxan derivatives - Google Patents

Process of stereoselective preparation of beta-phenylisoserin derivative and its use for preparation of taxan derivatives

Info

Publication number
CZ84095A3
CZ84095A3 CZ95840A CZ84095A CZ84095A3 CZ 84095 A3 CZ84095 A3 CZ 84095A3 CZ 95840 A CZ95840 A CZ 95840A CZ 84095 A CZ84095 A CZ 84095A CZ 84095 A3 CZ84095 A3 CZ 84095A3
Authority
CZ
Czechia
Prior art keywords
formula
pct
preparation
iii
beta
Prior art date
Application number
CZ95840A
Other languages
Czech (cs)
Other versions
CZ283290B6 (en
Inventor
Jean-Noel Denis
Andrew Greene
Alice Kanazawa
Original Assignee
Rhone Poulenc Rorer Sa
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Rhone Poulenc Rorer Sa filed Critical Rhone Poulenc Rorer Sa
Publication of CZ84095A3 publication Critical patent/CZ84095A3/en
Publication of CZ283290B6 publication Critical patent/CZ283290B6/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C27/00—Processes involving the simultaneous production of more than one class of oxygen-containing compounds
    • C07C27/20—Processes involving the simultaneous production of more than one class of oxygen-containing compounds by oxo-reaction
    • C07C27/22—Processes involving the simultaneous production of more than one class of oxygen-containing compounds by oxo-reaction with the use of catalysts which are specific for this process
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
    • C07D305/14—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Epoxy Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

PCT No. PCT/FR93/00966 Sec. 371 Date Apr. 5, 1995 Sec. 102(e) Date Apr. 5, 1995 PCT Filed Oct. 4, 1993 PCT Pub. No. WO94/07847 PCT Pub. Date Apr. 14, 1994This invention relates to a method of stereoselective preparation of a derivative of beta -phenylisoserine of formula (I) by the action of an N-carbonyl-benzylimine of formula (II) on an optically active amide of a protected hydroxyacetic acid of formula (III), followed by hydrolysis of the product obtained. In formula (I), (II) or (III), R is an optionally substituted phenyl radical or R1-O, Ar is an optionally substituted aryl radical and G1 is a hydroxy function protection grouping. The product of formula (I) is particularly useful in preparing taxol and Taxotere which have remarkable antitumor properties. <IMAGE> (I) ArCHNCOR (II) <IMAGE> (III)
CZ95840A 1992-10-05 1993-10-04 Process of stereoselective preparation of beta-phenylisoserine derivative and intermediate therefor CZ283290B6 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR9211740A FR2696454B1 (en) 1992-10-05 1992-10-05 Process for the stereoselective preparation of a beta-phenylisoserine derivative and its use for the preparation of Taxane derivatives.

Publications (2)

Publication Number Publication Date
CZ84095A3 true CZ84095A3 (en) 1995-09-13
CZ283290B6 CZ283290B6 (en) 1998-02-18

Family

ID=9434118

Family Applications (1)

Application Number Title Priority Date Filing Date
CZ95840A CZ283290B6 (en) 1992-10-05 1993-10-04 Process of stereoselective preparation of beta-phenylisoserine derivative and intermediate therefor

Country Status (23)

Country Link
US (2) US5726346A (en)
EP (1) EP0663901B1 (en)
JP (1) JPH08502051A (en)
KR (1) KR100290664B1 (en)
AT (1) ATE150451T1 (en)
AU (1) AU682011B2 (en)
CA (1) CA2146374A1 (en)
CZ (1) CZ283290B6 (en)
DE (1) DE69309086T2 (en)
DK (1) DK0663901T3 (en)
ES (1) ES2099479T3 (en)
FI (1) FI951589A0 (en)
FR (1) FR2696454B1 (en)
GR (1) GR3022872T3 (en)
HU (1) HUT73171A (en)
MX (1) MX9305765A (en)
NZ (1) NZ256444A (en)
PL (2) PL176503B1 (en)
RU (1) RU2109010C1 (en)
SK (1) SK280576B6 (en)
TW (1) TW436476B (en)
WO (1) WO1994007847A1 (en)
ZA (1) ZA937317B (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6025516A (en) * 1998-10-14 2000-02-15 Chiragene, Inc. Resolution of 2-hydroxy-3-amino-3-phenylpropionamide and its conversion to C-13 sidechain of taxanes
CA2385528C (en) 1999-10-01 2013-12-10 Immunogen, Inc. Compositions and methods for treating cancer using immunoconjugates and chemotherapeutic agents
US7601847B2 (en) 2004-10-26 2009-10-13 Wyeth Preparation and purification of 4-(indazol-3-yl)phenols
WO2010024762A1 (en) * 2008-08-26 2010-03-04 Organoclick Aktiebolag PREPARATION OF β-PHENYL-ISOSERINE DERIVATIVES
WO2010062239A1 (en) * 2008-11-03 2010-06-03 Cordova Armando A catalytic asymmetric method for the preparation of the paclitaxel (taxol) c-13 side-chain derivatives and its use in the preparation of taxane derivatives

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2629818B1 (en) * 1988-04-06 1990-11-16 Centre Nat Rech Scient PROCESS FOR THE PREPARATION OF TAXOL
CA2023645C (en) * 1989-08-23 2002-03-26 Jean-Noel Denis Process for the enantioselective preparation of phenylisoserin derivatives
FR2662441B1 (en) * 1990-05-22 1992-10-23 Rhone Poulenc Sante PROCESS FOR THE ENANTIOSELECTIVE PREPARATION OF PHENYLISOSERIN DERIVATIVES.
FR2662440B1 (en) * 1990-05-22 1992-07-31 Rhone Poulenc Sante PROCESS FOR THE STEREOSELECTIVE PREPARATION OF PHENYLISOSERIN DERIVATIVES.
US5684175A (en) * 1993-02-05 1997-11-04 Napro Biotherapeutics, Inc. C-2' hydroxyl-benzyl protected, N-carbamate protected (2R, 3S)- 3-phenylisoserine and production process therefor

Also Published As

Publication number Publication date
ZA937317B (en) 1994-04-22
NZ256444A (en) 1996-06-25
JPH08502051A (en) 1996-03-05
US5726346A (en) 1998-03-10
ATE150451T1 (en) 1997-04-15
FR2696454B1 (en) 1994-11-25
HU9500966D0 (en) 1995-06-28
MX9305765A (en) 1994-05-31
PL176503B1 (en) 1999-06-30
SK280576B6 (en) 2000-04-10
EP0663901B1 (en) 1997-03-19
DK0663901T3 (en) 1997-04-14
FR2696454A1 (en) 1994-04-08
PL308240A1 (en) 1995-07-24
EP0663901A1 (en) 1995-07-26
FI951589A (en) 1995-04-04
HUT73171A (en) 1996-06-28
RU2109010C1 (en) 1998-04-20
DE69309086T2 (en) 1997-09-25
DE69309086D1 (en) 1997-04-24
AU5114993A (en) 1994-04-26
KR100290664B1 (en) 2001-09-17
FI951589A0 (en) 1995-04-04
SK43795A3 (en) 1995-09-13
CA2146374A1 (en) 1994-04-14
PL173791B1 (en) 1998-04-30
AU682011B2 (en) 1997-09-18
CZ283290B6 (en) 1998-02-18
WO1994007847A1 (en) 1994-04-14
GR3022872T3 (en) 1997-06-30
KR950703499A (en) 1995-09-20
ES2099479T3 (en) 1997-05-16
US6114550A (en) 2000-09-05
RU95111377A (en) 1996-12-27
TW436476B (en) 2001-05-28

Similar Documents

Publication Publication Date Title
CA2146372A1 (en) New process for the esterification of baccatine iii and 10-desacetylbaccatine iii
AU5115193A (en) Method of preparing taxane derivatives
CA2146250A1 (en) Process for preparing taxane derivatives
DE69711391D1 (en) IMPROVED METHOD FOR PRODUCING PROTECTED 3,4-DIHYDROXYBUTTERIC ACID ESTERS
AU6207094A (en) Prodrug derivatives of enzyme inhibitors with hydroxyl groups, methods of preparing them and their use
HUT68540A (en) Process for preparing beta-phenylisoserine and analogues thereof
MX9307292A (en) REGIOSELECTIVE SYNTHESIS OF ACID 4-CHLORO-2-THIOPHENOCARBOXILICO.
CZ84095A3 (en) Process of stereoselective preparation of beta-phenylisoserin derivative and its use for preparation of taxan derivatives
FI955993A0 (en) Process for the preparation of N-acetylneuramic acid derivatives
AU7582396A (en) Synthesis of carboxylic acid derivatives

Legal Events

Date Code Title Description
IF00 In force as of 2000-06-30 in czech republic
MM4A Patent lapsed due to non-payment of fee

Effective date: 20031004